"Twenty years from now you will be more disappointed by the things you didn't do than by the ones you did do.

                   So throw off the bowlines, sail away from the safe harbor. Catch the trade winds in your sails."

                                                                                       - Mark Twain 

 

        Explore.    Dream.    Discover.

Charleston, South Carolina (20 offers included)

Tortola, Charleston, Newport & More
from $1,071.00 (USD)
Per Person
Mar 28, 2026
through Apr 06, 2026
Puerto Plata
Virgin Voyages logo
More offers from Virgin Voyages
Nights: 9
Ship: Valiant Lady
Price Per Night:$119.00 (USD)
(based on double occupancy, for comparison only)
Mar 28, 2026 through Apr 06, 2026
This 9-night one-way adventure departs from San Juan arriving the next day in Tortola. Then, spend a day at sea headed to Puerto Plata, DR, followed by two days sailing to a big city with even bigger Southern charm, Charleston, SC. From there, you'll spend the next day sailing to the classic architecture and quintessentially New England city Newport, Rhode Island before finally arriving in NYC.
Other Categories Starting At:
Inside
$1,071.00
Cat:IZ
119.00 per night
Outside
$1,251.00
Cat:VZ
139.00 per night
Balcony
$1,611.00
Cat:TZ
179.00 per night
Suite
$4,160.00
Cat:SS
462.22 per night
More Details Contact Us
Southern Charms
First-Class, Small Group Discovery
from $4,059.00 (USD)
Per Person
Oct 10, 2025
through Oct 18, 2025
Offer Image
Globus logo
More offers from Globus
Nights: 8
Price Per Night:$507.38 (USD)
(based on double occupancy, for comparison only)
Oct 10, 2025 through Oct 18, 2025
9 Days, featuring: Atlanta–columbia, South Carolina–charleston
More Details Contact Us
Bermuda Sunset & Southern Charm
12 nights on board Seven Seas Grandeur
from $8,799.00 (USD)
Per Person
Mar 26, 2026
through Apr 07, 2026
Offer Image
Regent Seven Seas Cruises logo
More offers from Regent Seven Seas Cruises
Nights: 12
Price Per Night:$733.25 (USD)
(based on double occupancy, for comparison only)
Mar 26, 2026 through Apr 07, 2026
Other Categories Starting At:
Outside
N/A
Balcony
N/A
Suite
$8,799.00
Cat:G2
733.25 per night
More Details Contact Us
19-Day Maple Explorer - Tour 2B
from $6,275.00 (USD)
Per Person
Oct 18, 2026
through Nov 06, 2026
Offer Image
Princess Cruises® logo
More offers from Princess Cruises®
Nights: 19
Price Per Night:$330.26 (USD)
(based on double occupancy, for comparison only)
Oct 18, 2026 through Nov 06, 2026
Other Categories Starting At:
Inside
$6,275.00
Cat:IF
330.26 per night
Outside
$6,885.00
Cat:OZ
362.37 per night
Balcony
$7,425.00
Cat:BF
390.79 per night
Suite
$8,525.00
Cat:ME
448.68 per night
More Details Contact Us
Canada & East Coast Explorer
Ft. Lauderdale to Toronto
from $7,995.00 (USD)
Per Person
Apr 22, 2027
through May 06, 2027
Offer Image
Viking Expeditions logo
More offers from Viking Expeditions
Nights: 14
Price Per Night:$571.07 (USD)
(based on double occupancy, for comparison only)
Apr 22, 2027 through May 06, 2027
Sail the US’s Atlantic coastline and visit storied cities. Enjoy Charleston’s southern charm and colonial homes. Visit Norfolk, home to the world’s largest naval base. Trace Nova Scotia’s shores to explore its rugged landscapes and visit Quebec’s national parks. Traverse one of North America’s scenic waterways, the St. Lawrence River, and marvel at the locks and canals that comprise the St. Lawrence Seaway on an enriching journey to historic ports.
Other Categories Starting At:
Inside
N/A
Outside
N/A
Balcony
$7,995.00
Cat:N2
571.07 per night
Suite
$10,995.00
Cat:NP
785.36 per night
More Details Contact Us
Southern Charm Holiday
Classic
from $2,999.00 (USD)
Per Person
Dec 02, 2025
through Dec 08, 2025
Offer Image
Collette logo
More offers from Collette
Nights: 6
Price Per Night:$499.83 (USD)
(based on double occupancy, for comparison only)
Dec 02, 2025 through Dec 08, 2025
Embrace the leisurely pace and charming allure of America’s southeast as you explore cobblestone streets, historic homes, and unspoiled coastline during the holiday season. Discover antebellum Charleston and the history of Savannah with 2-night stays in each city. Drive through James Island County Park illuminated with over 500,000 lights. Spend two nights at the exclusive Jekyll Island Club, once described as "the richest, most exclusive club in the world." Experience the unique charm and si...
More Details Contact Us
Southeast Coast & Bahamas
Roundtrip from Baltimore, Maryland
from $733.61 (USD)
Per Person
Mar 05, 2026
through Mar 13, 2026
Vision of the Seas in Norway
Royal Caribbean International logo
More offers from Royal Caribbean International
Nights: 8
Price Per Night:$91.70 (USD)
(based on double occupancy, for comparison only)
Mar 05, 2026 through Mar 13, 2026
Other Categories Starting At:
Inside
$733.61
Cat:ZI
91.70 per night
Outside
$813.61
Cat:YO
101.70 per night
Balcony
$1,563.11
Cat:XB
195.39 per night
Suite
N/A
More Details Contact Us
Southern Charm Holiday
Classic
from $3,299.00 (USD)
Per Person
Nov 30, 2026
through Dec 06, 2026
Offer Image
Collette logo
More offers from Collette
Nights: 6
Price Per Night:$549.83 (USD)
(based on double occupancy, for comparison only)
Nov 30, 2026 through Dec 06, 2026
Embrace the leisurely pace and charming allure of America’s southeast as you explore cobblestone streets, historic homes, and unspoiled coastline during the holiday season. Discover antebellum Charleston and the history of Savannah with 2-night stays in each city. Drive through James Island County Park illuminated with over 500,000 lights. Spend two nights at the exclusive Jekyll Island Club, once described as "the richest, most exclusive club in the world." Experience the unique charm and si...
More Details Contact Us
World Odyssey
Los Angeles to Miami
from $75,999.00 (USD)
Per Person
Dec 20, 2025
through Jul 05, 2026
Offer Image
Oceania Cruises logo
More offers from Oceania Cruises
Nights: 197
Ship: Vista
Price Per Night:$385.78 (USD)
(based on double occupancy, for comparison only)
Dec 20, 2025 through Jul 05, 2026
Other Categories Starting At:
Inside
N/A
Outside
N/A
Balcony
$75,999.00
Cat:B2
385.78 per night
Suite
N/A
More Details Contact Us
From the Arctic to Antarctica
Nuuk to Ushuaia
from $76,995.00 (USD)
Per Person
Sep 03, 2025
through Nov 28, 2025
Offer Image
Viking Expeditions logo
More offers from Viking Expeditions
Nights: 86
Price Per Night:$895.29 (USD)
(based on double occupancy, for comparison only)
Sep 03, 2025 through Nov 28, 2025
Witness stunning vistas, unique wildlife and diverse cultures as you journey on a memorable voyage from the Earth’s far north to the extreme south. Admire Nuuk’s rugged beauty and the icy wilderness of the Canadian High Arctic. Pass through the scenic Canadian Maritimes, sail along the famed St. Lawrence Seaway and visit historic cities along the East Coast. Navigate the striking Chilean Fjords, before exploring the icy realm of Antarctica.
Other Categories Starting At:
Inside
N/A
Outside
N/A
Balcony
$76,995.00
Cat:DN3
895.29 per night
Suite
N/A
More Details Contact Us
Southeast Coast & Bahamas
Roundtrip from Baltimore, Maryland
from $784.66 (USD)
Per Person
Feb 13, 2026
through Feb 21, 2026
Vision of the Seas in Norway
Royal Caribbean International logo
More offers from Royal Caribbean International
Nights: 8
Price Per Night:$98.08 (USD)
(based on double occupancy, for comparison only)
Feb 13, 2026 through Feb 21, 2026
Other Categories Starting At:
Inside
$784.66
Cat:ZI
98.08 per night
Outside
$914.16
Cat:YO
114.27 per night
Balcony
$1,654.66
Cat:1B
206.83 per night
Suite
N/A
More Details Contact Us
Southeast Coast & Bahamas Holiday
Roundtrip from Baltimore, Maryland
from $1,023.71 (USD)
Per Person
Dec 19, 2025
through Dec 27, 2025
Vision of the Seas in Norway
Royal Caribbean International logo
More offers from Royal Caribbean International
Nights: 8
Price Per Night:$127.96 (USD)
(based on double occupancy, for comparison only)
Dec 19, 2025 through Dec 27, 2025
Other Categories Starting At:
Inside
$1,023.71
Cat:ZI
127.96 per night
Outside
$1,163.71
Cat:YO
145.46 per night
Balcony
$1,751.21
Cat:3B
218.90 per night
Suite
N/A
More Details Contact Us
Fall Leaves to Miami Scenes
from $1,027.00 (USD)
Per Person
Oct 03, 2025
through Oct 16, 2025
Offer Image
Virgin Voyages logo
More offers from Virgin Voyages
Nights: 13
Price Per Night:$79.00 (USD)
(based on double occupancy, for comparison only)
Oct 03, 2025 through Oct 16, 2025
This 13-night north-to-south sojourn departs from Quebec and over to Halifax, Nova Scotia - the lobster capital of the world - for a day of outdoor adventures. Next, cross the breathtaking Bay of Fundy, and onward to Eastport, Maine. Soak up the blissful sea day in between stops to two of the U.S.'s most historic (and oldest) cities, Boston and Charleston, before ending on the shores of Miami.
Other Categories Starting At:
Inside
$1,027.00
Cat:IZ
79.00 per night
Outside
$1,287.00
Cat:VZ
99.00 per night
Balcony
$1,417.00
Cat:TZ
109.00 per night
Suite
$4,927.00
Cat:RZ
379.00 per night
More Details Contact Us
Southeast Coast & Bahamas
Roundtrip from Baltimore, Maryland
from $849.72 (USD)
Per Person
Nov 21, 2025
through Nov 29, 2025
Vision of the Seas in Norway
Royal Caribbean International logo
More offers from Royal Caribbean International
Nights: 8
Price Per Night:$106.22 (USD)
(based on double occupancy, for comparison only)
Nov 21, 2025 through Nov 29, 2025
Other Categories Starting At:
Inside
$849.72
Cat:3V
106.22 per night
Outside
$949.22
Cat:3N
118.65 per night
Balcony
$1,771.72
Cat:1B
221.47 per night
Suite
N/A
More Details Contact Us
Canada & East Coast Explorer
Toronto to Ft. Lauderdale
from $9,995.00 (USD)
Per Person
Oct 09, 2026
through Oct 23, 2026
Offer Image
Viking Expeditions logo
More offers from Viking Expeditions
Nights: 14
Price Per Night:$713.93 (USD)
(based on double occupancy, for comparison only)
Oct 09, 2026 through Oct 23, 2026
Sail the US’s Atlantic coastline and visit storied cities. Enjoy Charleston’s southern charm and colonial homes. Visit Norfolk, home to the world’s largest naval base. Trace Nova Scotia’s shores to explore its rugged landscapes and visit Quebec’s national parks. Traverse one of North America’s scenic waterways, the St. Lawrence River, and marvel at the locks and canals that comprise the St. Lawrence Seaway on an enriching journey to historic ports.
Other Categories Starting At:
Inside
N/A
Outside
N/A
Balcony
$9,995.00
Cat:N2
713.93 per night
Suite
$12,995.00
Cat:NP
928.21 per night
More Details Contact Us
Southern Charms: St. Augustine, Savannah & Charleston
Land Journey
from $5,290.00 (USD)
Per Person
Mar 25, 2026
through Apr 01, 2026
Offer Image
Tauck logo
More offers from Tauck
Nights: 7
Price Per Night:$755.71 (USD)
(based on double occupancy, for comparison only)
Mar 25, 2026 through Apr 01, 2026
Evoking long-ago days of gracious Southern living, this Tauck journey explores National Historic Landmark Districts in Savannah, Charleston and Beaufort; Low Country folkways; the legacy of the Mighty 8th Air Force and more. Enjoy private dinners... a private Charleston harbor cruise... visits to plantations, gardens and a Civil War fort... and time in historic St. Augustine.
More Details Contact Us
Southern Charm featuring Charleston, Savannah & Jekyll Island
Classic
from $2,999.00 (USD)
Per Person
Apr 28, 2026
through May 04, 2026
Offer Image
Collette logo
More offers from Collette
Nights: 6
Price Per Night:$499.83 (USD)
(based on double occupancy, for comparison only)
Apr 28, 2026 through May 04, 2026
Embrace the leisurely pace and charming allure of America’s southeast as you explore cobblestone streets, historic homes, and unspoiled coastline. Discover antebellum Charleston and the history of Savannah with 2-night stays in each city. Visit Charleston’s City Market, one of the oldest public markets in America. Enjoy a trolley or walking tour of Savannah's sprawling Historic District. Spend two nights at the exclusive Jekyll Island Club, once described as "the richest, most exclusive club ...
More Details Contact Us
Antilles & Atlantic Gems
Roundtrip from Miami
from $10,999.00 (USD)
Per Person
Mar 09, 2026
through Apr 04, 2026
Oceania Allura
Oceania Cruises logo
More offers from Oceania Cruises
Nights: 26
Ship: Allura
Price Per Night:$423.04 (USD)
(based on double occupancy, for comparison only)
Mar 09, 2026 through Apr 04, 2026
Other Categories Starting At:
Inside
N/A
Outside
N/A
Balcony
$10,999.00
Cat:B4
423.04 per night
Suite
$16,199.00
Cat:PH2
623.04 per night
More Details Contact Us
Southern Charm featuring Charleston, Savannah, and Jekyll Island
Classic
from $3,299.00 (USD)
Per Person
May 25, 2026
through May 31, 2026
Offer Image
Collette logo
More offers from Collette
Nights: 6
Price Per Night:$549.83 (USD)
(based on double occupancy, for comparison only)
May 25, 2026 through May 31, 2026
Embrace the leisurely pace and charming allure of America’s southeast as you explore cobblestone streets, historic homes, and unspoiled coastline. Discover antebellum Charleston and the history of Savannah with 2-night stays in each city. Visit Charleston’s City Market, one of the oldest public markets in America. Enjoy a trolley or walking tour of Savannah's sprawling Historic District. Spend two nights at the exclusive Jekyll Island Club, once described as "the richest, most exclusive club ...
More Details Contact Us
Canada & East Coast Explorer
Toronto to Ft. Lauderdale
from $8,995.00 (USD)
Per Person
Sep 22, 2025
through Oct 06, 2025
Offer Image
Viking Expeditions logo
More offers from Viking Expeditions
Nights: 14
Price Per Night:$642.50 (USD)
(based on double occupancy, for comparison only)
Sep 22, 2025 through Oct 06, 2025
Sail the US’s Atlantic coastline and visit storied cities. Enjoy Charleston’s southern charm and colonial homes. Visit Norfolk, home to the world’s largest naval base. Trace Nova Scotia’s shores to explore its rugged landscapes and visit Quebec’s national parks. Traverse one of North America’s scenic waterways, the St. Lawrence River, and marvel at the locks and canals that comprise the St. Lawrence Seaway on an enriching journey to historic ports.
Other Categories Starting At:
Inside
N/A
Outside
N/A
Balcony
$8,995.00
Cat:N2
642.50 per night
Suite
$12,495.00
Cat:NP
892.50 per night
More Details Contact Us